title: Anthocyanin-derived phenolic acids form glucuronides following simulated gastrointestinal digestion and microsomal glucuronidation.
abstract: METHODS
  Current research indicates that anthocyanins are primarily degraded to form phenolic acid products. However, no studies have yet demonstrated the metabolic conjugation of these anthocyanin-derived phenolic acids in humans.
  
  
  RESULTS
  Within the present study, a simulated gastrointestinal digestion model was used to evaluate the potential degradation of anthocyanins post-consumption. Subsequently, cyanidin (Cy) and pelargonidin and their degradation products, protocatechuic acid and 4-hydroxybenzoic acid, were incubated in the presence of human liver microsomes to assess their potential to form hepatic glucuronide conjugates. For structural conformation, phenolic glucuronides were chemically synthesised and compared to the microsomal metabolites. During the simulated gastric digestion, anthocyanin glycosides (200 μM) remained stable however their aglycone derivatives were significantly degraded (20% loss), while during subsequent pancreatic/intestinal digestion only pelargonidin-3-glucoside remained stable while cyanidin-3-glucoside (30% loss) and Cy and pelagonidin aglycones were significantly degraded (100% loss, respectively). Following microsomal metabolism, pelargonidin formed 4-hydroxybenzoic acid, which was further metabolised (65%) to form two additional glucuronide conjugates, while Cy formed protocatechuic acid, which was further metabolised (43%) to form three glucuronide conjugates.
  
  
  CONCLUSIONS
  We propose that following ingestion, anthocyanins may be found in the systemic circulation as free or conjugated phenolic acids, which should be a focus of future dietary interventions.
authors.affiliation: School of Medicine, University of East Anglia, Norwich, UK.
authors.forename: Gary M
authors.initials: GM
authors.lastname: Woodward
authors.forename: Paul W
authors.initials: PW
authors.lastname: Needs
authors.forename: Colin D
authors.initials: CD
authors.lastname: Kay
mesh_terms: D000704:Analysis of Variance; D000872:Anthocyanins / Q000378:metabolism*; D002851:Chromatography, High Pressure Liquid; D004063:Digestion; D005960:Glucosides / Q000378:metabolism*; D020719:Glucuronides / Q000138:chemical synthesis / Q000378:metabolism*; D006801:Humans; D062385:Hydroxybenzoates / Q000138:chemical synthesis / Q000378:metabolism*; D007413:Intestinal Mucosa / Q000378:metabolism; D008297:Male; D008862:Microsomes, Liver / Q000378:metabolism*; D010226:Parabens / Q000378:metabolism
chemical_list: D000872:Anthocyanins; D005960:Glucosides; D020719:Glucuronides; D062385:Hydroxybenzoates; D010226:Parabens; C462279:cyanidin-3-O-beta-glucopyranoside; C009091:protocatechuic acid; C066957:pelargonidin; C017154:cyanidin; C078485:pelargonidin-3-glucoside; C017616:phenolic acid; C038193:4-hydroxybenzoic acid